Ruin Your Life (And 21 Other Tips About Writing)

I took LSD and it ruined my life. This is not a writing tip.

I was at graduate school in 1990 and I wanted to be a professor of Computer Science. I took one tab.

Nothing was happening. Then suddenly we were lying on the floor and the ceiling was a maze. Then suddenly we were looking at trees and every leaf was talking to me. Then suddenly people were looking at me and laughing.

Then suddenly then suddenly then suddenly it was the worst day of my life and I knew I had six hours left before the world would stop roaring in my head.

Then suddenly I wanted to be a writer.

I stopped going to class. I still cashed my scholarship check though. I’d get emails from professors, “Where are you?”

I started writing every day. I was thrown out of graduate school. My parents cried. End of career.

Eighteen years later I write every day.

My parents cried.


I wrote a play when I was seven (my teacher had everyone in the class read it and they all laughed at me – a common theme in my life).

In fifth grade I was writing a book, “Who Likes Who?” about all the kids in my class and which boys liked which girls.

Everyone wanted to read it. It would’ve been a bestseller in my fifth grade class.

Fights broke out as kids tore at each other and me trying to get the book. The teacher banned it.

In 8th grade I got my first book deal. To write a book about how to solve a Rubik’s Cube. I was obsessed with Rubik’s Cube. So obsessed I got everyone else obsessed and then they banned it from school. Censorship struck again!

I never wrote the book. No discipline.

And then, years later, LSD.

The next day I was a writer. I wrote a story about a man finding out his girlfriend cheated so he gets AIDS (magically) and then has sex with her and she now has AIDS.

It was horrible.

I gave it to my friends to read. They didn’t say anything. They looked at each other. One of them said to me, “Well… how do YOU feel about this story?”

One time I bombed at stand-up comedy. I asked my friends if they enjoyed the show and they said to me, “Well… did YOU enjoy the show?”


I wrote a novel, “The Book of Orpheus” (about a man who creates an artificial currency). I was influenced by Thomas Pynchon’s “The Crying of Lot 49” about a secret postal service.

I read. I read and I read.

[“So, you read a lot of books?”]

I read at least four hours a day. Then I’d go to the library and there was this series of books, “The Encyclopedia of Literary Criticism” and I’d read all the criticism on the books I just read

I wrote another novel, “The Book of David” (I liked “The Book of…”) about a fictional version of King David. It was 500 pages. My girlfriend would beg me to stop talking about it.

She read it when it was done. I asked her what she thought of the ending. She couldn’t remember the ending and started crying.

I wrote a novel, “The Porn Novelist, The Romance Novelist, The Prostitute, and They’re Lovers”. I wrote it in three days. It was 150 pages.

I went to my new girlfriend’s house and gave it to her to read. She wouldn’t take it. She wouldn’t open the door.

She said, “I thought we were taking a break!”


I wrote another novel, “How to Save the World from Mutual Assured Destruction”.

I made it a three inch book that you could read and then turn upside down and read the other way. I printed up 300 copies and gave them to bookstores to sell for 25 cents.

If anyone has one, I’ll pay $10,000 for it.

I wrote dozens of short stories. I wrote for HBO’s website. I wrote and wrote and wrote. I wrote 3,000 words a day every day and still do.

I got nothing published at all for 12 years. I sent out thousands of letters. Please please publish this!

Nothing. Not even a response.


Some people get things published right away. But I was a very bad writer.

I don’t know if I was resilient, persistent, or stupid. You have to be a little stupid and arrogant to want to be good at writing.

Because when you start, you suck by definition. It’s a very hard skill. At least for me.

And you have to be arrogant to write, because who wants to hear what you have to say?

The first article I got paid for was in 2003. I got $200.

I got that check, walked a mile to a frame store in the middle of a blizzard. Got the check framed.

“Don’t you want to cash it?”

No. I want you to frame it.

I threw it out in 2015 along with everything else I owned in life.

My first book was in 2004. I got fired when the book was published. My boss thought I gave away all his secrets.

My second published book was in 2005. Third in 2006. Fourth in 2008. Fifth in 2009. 2010. 2011. 2012. 2013 (“Choose Yourself!” which has sold over a million copies). 2014. 2015. 2016. 2018 (two books coming out next month to make up for 2017, when I focused on getting better at stand-up comedy).

(Published in about 30 countries. This is “Choose Yourself” in Turkey)

I became friends with many writers. They’ve saved me over and over again.

Writing is also a great way to make enemies. If people hate what you write then they hate you. My mother and sister don’t talk to me.

I’ve published 21 books. Some by mainstream publishers, some self-published, some published just to my email list (“FAQ ME TOO”).

I’ve published over 5,000 articles or posts.

I’ve written articles that have gotten thousands of hate comments: “Why no war can be justified”, “Why I will never own a house again”, “Why you shouldn’t send your kids to college”.

I’ve written articles that have made me happy with the praise: “How to be the luckiest man in the world” and one person wrote in the comments, “the internet was created just so this article could exist”.

Worst comment: “I wish I could put this jew in a wheat thresher and tear him to shreds”.

I reported that comment to campus security at [Ivy League University] and they said, “The kid’s about to graduate. Do you really want to hurt his career?”

I’ve published a novel, a comic book, a children’s book (“My Daddy Owns All of Outer Space”), investment books, and many “literary non-fiction” books.

(Here’s the link to my children’s book trailer)


(Comic book)

I wrote a screenplay last year (nobody liked it) about a hedge fund manager who secretly wants to be a stand-up comedian. A few months later, “The Marvelous Mrs. Maisel” came out and people thought it was too similar.

I start a novel at least once a year and never finish them.

I’m a student. I’m reading a novel right now that makes me gasp at his use of language.

I bring my favorite novelists onto my podcast just so I can ask hundreds of questions about their process (Mary Karr, Judy Blume, Ken Follett, Brad Meltzer, James Frey, Jim Luceno, Andy Weir, Hugh Howey, and hundreds of other fiction, TV, and non-fiction writers that are all my heroes).

(Whenever I reread “A Million Little Pieces” by James Frey (above), I become a better writer)

I read thrillers to learn about cliffhangers and plot.

I read literary novels to learn about structure and words and colors.

I read memoirs to absorb other lives.

I read essays to read how people play with words and structure to express ideas.

I’m a student. I want to write a sentence that will make people go through the five stages of grief in one second.

I want to write because I’m insecure and want more people to like me.

I’m going to die before I write the book I want to write.

I hate typing. I hate staring at a screen. I hate writing 70 pages and then realizing it was all useless. I hate writing.

I love when my kids read what I write even when they find out the worst things about me. I hate when I reveal so much that people stop talking to me.

(My kids wearing “Choose Yourself” t-shirts. All 65,000 words are printed on the shirt and it’s totally readable)

I’ve wasted so much time writing these past 28 years. And for what?

I pray to god I still have the strength and discipline and love to write tomorrow.

I don’t have that strength though. I don’t know. I’ll find out tomorrow.

There are no tips other than to write write write. And read read read. There are no other tips.

But here are some tips:

  • Read “Old Man and the Sea” – Read it once a year. Read how he strips out every word. It’s the most boring story in the world. It’s written at a fourth grade level. But every time I read it I become (I think I hope) a better writer.
  • Obvious: Write every day.
  • Read “Factotum” by Charles Bukowski (the art of the short chapter. The art of the memoir novel. The art of being bad but being lovable. The art of being depressed and scared and hopeless but sharing it).

(Bukowski teaches how to make Ugly, Beautiful)

  • Read “A Million Little Pieces” by James Frey (the sentences!) and “Spectacle” by Susan Steinberg (you will be one writer before you read it and a different one after you read it). And, most important, I’ve read “Jesus’ Son” by Denis Johnson at least 300 times and I will read it 300 more times.
  • No matter what you write in the first draft, cut out 30% by the final draft.
  • No matter what you write, before you are done, take out the first and last paragraph. Even if you know this rule, it still works.
  • The best marketing for a book is write the next book.
  • Avoid adjectives and adverbs. The story should reveal how quick he ran. Not the word “quick”.
  • Try for a cliffhanger every paragraph. Fiction or non-fiction.
  • Take a s**t before you start writing.
  • Short paragraphs.
  • Go to the place least crowded.
  • Be an addict of writing.

(She is an example of the last two tips. She also signed up for a dating site I once created for smokers only. A bad idea)

  • Bleed in the first line, even if you have to start in the middle of a story.
  • ABS = Always be Stupid. Never lecture. That automatically puts you in the top 1% of writers. Show how incompetent are and yet…we’re all still here.
  • Arc of the Hero: Ordinary world, Call to Action, Mentor, Find Enemies and Friends, Bigger and bigger problems, Final cliffhanging, life-changing moment, Return to the World (with one final problem solved), The hero is back and changed. Every story needs this.
  • Idea Sex: Take one idea, combine it with another idea. BOOM! Thrillers + Legal = John Grisham selling 200 million books.
  • Write down ten ideas a day. Get’s the juices flowing.

(Doesn’t matter what the ideas are. Just exercise the thinking muscles. I write them each day on a waiter’s pad since 2002)

  • Study the Arc of the Hero structure in: the Bible, Star Wars, Spiderman, a Math textbook. Whatever else you want.
  • Write Read Steal Repeat. Steven Pressfield stole “The Bhavagad Gita” and put the exact structure in a novel about golf in the 1930s. “The Legend of Bagger Vance” is now a modern classic.
  • Process is all that matters. Outcomes will take care of themselves.

Love other people. The only story is about love.

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